CLASSIC TUSCANY
Chianti Vacation Rentals
Chianti is the classic area of Tuscany that many dream of visiting. Renting a villa in Chianti positions you at the epicenter of Italy’s most famous wine region amidst heartbreakingly beautiful scenery. Charming medieval hill towns reveal ancient churches and castles, surrounded by the classic Tuscan landscape of rustic farmhouses tucked among its hills. Visit Siena, Florence, San Gimignano, Volterra, Greve or Panzano. Follow the ancient wine road that runs between Florence and Siena — stopping at vineyards along the way for tours and tastings. From your Chianti villa, you’ll instantly appreciate how the region today epitomizes all that Tuscany represents as a land of inexhaustible culinary, cultural and historical fascination—along with jaw-dropping natural beauty.
Villa Amarika
7 bed, 7 bath, from €30,715/week
Villa Amarika is a great choice for large groups who want to get a glimpse of true Tuscan life. The villa is jsut 50 minutes from Florence and 25 minutes from Siena, the iconic views of Tuscany.
Villa La Tavernaccia
8 bed, 7.5 bath, from €30,300/week
Dream Renaissance villa in heart of Tuscany. Luminous, luxurious, and relaxing. The setting is picture perfect — a classic Renaissance villa set on a hill and commanding an impressive view over the gorgeous Tuscan countryside.
Villa Colli
7 bed, 7 bath, from €17,545/week
I Colli is the perfect vacation villa for families and groups of friends. The villa has many gathering spaces, outdoor and indoor, perfect for hosting dinners and parties, and the heated pool makes it a great off-season retreat.
Villa Trionfante
7 bed, 7 bath, from €28,570/week
The layout with two separate annexes gives space to the group without the risk of overcrowding. Enjoy the privacy of the estate, including a private access to the nearby river. Florence is just 25 minutes away.
Villa Il Casolare
5 bed, 5 bath, from €21,000/week
Il Casolare is a not a typical Tuscan farmhouse. Instead it is a 5-star, 3800 sq ft luxury farmhouse sitting on 124 acres for people who want to pamper themselves. Our guests rave about the owner’s hospitality and the villa’s beauty.
Villa Danica
5 bed, 5 bath, from €17,550/week
Surrounded by soft rolling hills and glorious views, Danica has been meticulously restored to create the perfect scenario for a vacation you will never forget.The villa, with an eclectic and relaxed design, offers a true respite from everyday life.
Villa Morea
6 bed, 5 bath, from €10,000/week
Villa Morea offers high-end interiors, landscaped gardens, furnished outdoor spaces and enchanting views from its stone-paved pool. This villa is ideal for multi-generational reunions in Tuscany.
Villa La Fontenella
5 bed, 7 bath, from €10,780/week
Villa La Fontenella is located in the heart of Tuscany's Chianti region, with expansive views over the olive groves. The location couldn’t be better: private, tranquil position on hillside just 15 minutes south of Florence.
Villa La Novellina
5 bed, 5 bath, from €9,040/week
La Novellina is a wonderfully renovated farmhouse built around a central 11th-century tower and located halfway between Florence and Siena, overlooking the Chianti hills.This typical Tuscan house has been respectfully restored.
Villa Certaldo
13 bed, 13 bath, rates on request
Villa Certaldo is a beautiful estate overlooking the vast hills of Tuscany. The estate consists of ten apartments (six of which are air conditioned), and is perfect for large groups. Many beautiful weddings have been held at the villa over the years.
Villa Hortus
5 bed, 5 bath, rates on request
Enjoy the unspoiled Tuscan countryside in this authentic yet modern villa. While retaining its original structure, Villa Hortus offers contemporary amenities that cater to modern comforts. This impeccably designed home offers lush surroundings, an infinity pool, and plenty of common spaces
Villa Poggio delle Rose
11 bed, 11 bath, rates on request
Poggio delle Rose is an elegant hilltop farmstead, strategically positioned in the center of the Golden Triangle between Florence, Siena and Pisa. The property sits on top of a hill, surrounded by 24 acres or vineyards, olive groves and woods.
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